Cyclopentanol → Cyclopentyl 4-methylbenzene-1-sulfonate

HRID 1684323Notes

Reaction equation

HRID 1684323 reaction equation
[CH:1]1([OH:6])[CH2:5][CH2:4][CH2:3][CH2:2]1.[C:7]1([CH3:17])[CH:12]=[CH:11][C:10]([S:13](Cl)(=[O:15])=[O:14])=[CH:9][CH:8]=1.[OH-].[K+]>CCOCC>[C:7]1([CH3:17])[CH:12]=[CH:11][C:10]([S:13]([O:6][CH:1]2[CH2:5][CH2:4][CH2:3][CH2:2]2)(=[O:15])=[O:14])=[CH:9][CH:8]=1

Participants

5

Reactant 3

HCID 7298CyclopentanolHCID 73974-Toluenesulfonyl chlorideHCID 14797Potassium Hydroxide

Product 1

HCID 317685Cyclopentyl 4-methylbenzene-1-sulfonateYield 78.9%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A round-bottomed flask (200 cc) was charged with cyclopentyl alcohol (10.0 g, 0.116 mol) and p-toluenesulfonyl chloride (24.3 g, 0.128 mol), followed by the addition of ether (100 mL) to form a solution. Subsequently, a powder of potassium hydroxide (32.5 g, 0.58 mol) was added slowly to the solution as it was cooled in a water bath at 10° C. or below. After the addition, the mixture was stirred at the same temperature for an additional 2 h. After completion of the reaction, the mixture was poured into ice water (20 mL), whereupon the organic layer separated from the aqueous layer. The organic layer was dried and concentrated under vacuum to give cyclopentyl p-toluenesulfonate as a pale yellow viscous liquid (22.0 g; yield=78.9%).

Workup

  1. customto form a solution
  2. temperaturewas cooled in a water bath at 10° C. or below
  3. additionAfter the addition
  4. customAfter completion of the reaction
  5. customseparated from the aqueous layer
  6. customThe organic layer was dried
  7. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-ddd90fa504fb42b3b474a0d2053d3403
Source dataset
uspto-grants-1997_06
Patent number
US05639915

Reaction notes

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